Hydrochloric Acid → HCID 60207421, compound

HRID 1192202Notes

Reaction equation

HRID 1192202 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:29]([O-:31])=[O:30].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][NH:19][CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:29]([O-:31])=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60207420HCID 60207420, compound

Product 1

HCID 60207421HCID 60207421, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

tert-butyl 3-(5-((3,5-dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxamido)pyrrolidine-1-carboxylate (3.0 g, 5.63 mmol) from the above was added to a solution of hydrogen chloride in ethanol (2.0 M, 20 mL) and ethanol (30 mL), and the resulting mixture was stirred at ambient temperature for 4 hours. After this time, the mixture was concentrated, washed with dry ether and dried in vacuo overnight to afford the title product as a white solid (2.2 g, 91% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, m), 8.86 (1H, d), 8.78 (1H, m), 8.50 (1H, s), 4.20 (1H, m), 2.94 (2H, m), 2.79 (1H, m), 2.67 (1H, m), 1.93 (1H, m), 1.67 (1H, m). MS m/z: 419.20, 421.20 [M+H]+.

Workup

  1. concentrationAfter this time, the mixture was concentrated
  2. washwashed with dry ether
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-5075e8eda92640b7884f243072e2e8b4
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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